This paper intends to show the processes and identity negotiations of white working-class boys surrounding their own learner-identity within a "raising aspirations" rhetoric. The current dominant neoliberal discourse, which prioritizes a view of aspiration that is competitive, economic, and status-based, shapes the subjectivities of these young males. Focusing on the deeply engrained values of a group of 23 working-class boys from South London, ages 14-16, this research critically considers the conception of aspiration and persistent "educational underachievement". White working-class boys in the United Kingdom are frequently labelled as having "low aspirations" or, indeed, no aspirations at all. Through the use of habitus as a conceptual tool, the research intends to serve as an exploration of how the aspiration rhetoric influenced the boys' conception of "loyalty to self" and their sense of average-ness/ordinariness/"middling". The boys' habitus undergoes complex "identity work" in order to reconcile competing and contrasting conceptions of aspiration.